ETUDE D'UN MODELE D'INDUCTION ASYMETRIQUE: LES OXAZOLIDINES α,β-INSATUREES ISSUES DE L'EPHEDRINE
Various oxazolidines were prepared from ephedrine.It was shown that their formation is not general, the reaction is not always stereoselective and can lead to isomerization of the double bond of α,β-unsaturated aldehydes.Some of these oxazolidines were used in stereoselective preparation of β-alkyl aldehydes.
Mangeney, P.,Alexakis, A.,Normant, J.F.
p. 1803 - 1808
(2007/10/02)
ADDITION DIASTEREOSELECTIVE D'ORGANOCUPRATES A UNE OXAZOLIDINE CHIRALE α,Β INSATUREE: EFFET DE SOLVANT ET APPLICATION DES RESULTATS DE LA RMN 1H A LA DETERMINATION DE LA CONFIGURATION ABSOLUE ET DE LA PURETE OPTIQUE D'ARYL-3-ALKANALS
Addition of lithium dimethylcuprate to the chiral oxazolidine (1) in ether or in hexane leads to 3-phenylbutanals having the S or R configuration, respectively, with high optical yield in the latter case (e.e. = ca. 80percent).The 1H NMR study of the intermediate oxazolidine allows accurate determination of the optical yield and could be applied to the determination of the absolute configuration and optical purity of other 3-arylalkanals.
Berlan, J.,Besace, Y.,Prat, D.,Pourcelot, G.
p. 399 - 408
(2007/10/02)
Synthese asymetrique d'aldehydes a partir d'oxazolidines chirales α,β-insaturees et d'organocuprates
Oxazolidines derived from α,β-ethylenic aldehydes and (+) or (-) ephedrines react with organocuprates to yield optically active aldehydes.
Mangeney, P.,Alexakis, A.,Normant, J. F.
p. 373 - 374
(2007/10/02)
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